Holiday Homes in Shirley

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Check prices for these dates

Our top choices for Shirley holiday homes

1. 3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (24 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is AU$972
includes taxes & fees
17 Nov - 18 Nov
3 Story Beach Waterview, 3 KING bed, golf putting green!

2. Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
9.8 out of 10, Exceptional, (7 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is AU$785
includes taxes & fees
15 Nov - 16 Nov
Modern Vacation home. Close to The Hamptons

3. Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (34 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is AU$2,146
includes taxes & fees
2 Dec - 3 Dec
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

4. Peaceful 3BR Garden Cottage Long Island Escape

Peaceful 3BR Garden Cottage Long Island Escape
Coram
10.0 out of 10, Exceptional, (1 review)
"Excellent host and peaceful getaway. I highly recommend!"
United States
Greg M.
The price is AU$677
includes taxes & fees
15 Nov - 16 Nov
Peaceful 3BR Garden Cottage Long Island Escape

5. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (10 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$483
includes taxes & fees
25 Nov - 26 Nov
The Royal Suite - Ronkonkoma

6. Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (57 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is AU$253
includes taxes & fees
15 Nov - 16 Nov
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

7. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is AU$1,660
includes taxes & fees
16 Nov - 17 Nov
Jacuzzi year-round - Villa Luz Private Home

8. Prime location, walk to all, cozy cottage Westhampton Beach

Prime location, walk to all, cozy cottage Westhampton Beach
Westhampton Beach
10.0 out of 10, Exceptional, (4 reviews)
"Property was in easy walking distance from the village which made morning coffee runs a breeze. Very clean accommodations and large back yard."
United States
Matt S.
The price is AU$849
includes taxes & fees
24 Nov - 25 Nov
Prime location, walk to all, cozy cottage Westhampton Beach

9. Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
8.8 out of 10, Excellent, (8 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is AU$331
includes taxes & fees
18 Nov - 19 Nov
Peaceful private 2-bedroom house in Bayport. Amazing location!

10. Long Island 2BR Garden Suite + Private Dry Sauna & Ping Pong

Long Island 2BR Garden Suite + Private Dry Sauna & Ping Pong
Central Islip
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, clean and inviting space. Thanks for a great space away from home; will definietly book again."
United States
Vladamir R.
Long Island 2BR Garden Suite + Private Dry Sauna & Ping Pong

11. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"What an amazing view!!!!! Great place to stay!!! Highly recommend the Black Swan home."
United States
John M.
The price is AU$1,759
includes taxes & fees
15 Nov - 16 Nov
Beachfront Jacuzzi All Year - Black Swan Home

12. Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (29 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is AU$757
includes taxes & fees
18 Nov - 19 Nov
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

13. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AU$467
includes taxes & fees
19 Nov - 20 Nov
Spacious 3BR Family Home Near Everything

14. Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
7.8 out of 10, Good, (13 reviews)
"Very responsive host and a beautiful house."
United States
Robin M.
The price is AU$888
includes taxes & fees
18 Nov - 19 Nov
Cozy beach hose minutes from Hamptons

15. Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
9.2 out of 10, Wonderful, (13 reviews)
"Super close to everything and the host was very communicative. Overall, a great experience."
United States
Melissa G.
The price is AU$1,152
includes taxes & fees
26 Nov - 27 Nov
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

16. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (6 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is AU$3,734
includes taxes & fees
15 Nov - 16 Nov
5 Bedrooms! 4 Min to the Beach! HEATED POOL!

17. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is AU$467
includes taxes & fees
29 Nov - 30 Nov
Sundown Escape Near SouthShore University Hospital

18. Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
8.8 out of 10, Excellent, (3 reviews)
"My stay was amazing! The place was bigger in person than i expected, which was such a pleasant surprise. The house was spotless and very clean, making me feel comfortable from the moment I arrived. The host was incredibly helpful, responsive, and made the entire experience smooth and stress-free. I enjoyed my stay and would absolutely book this home again. Highly recommend to anyone looking for a clean, spacious, and welcoming place to stay!"
United States
Tatiana J.
The price is AU$669
includes taxes & fees
23 Nov - 24 Nov
Bright & Comfortable Home in the Heart of It All

19. Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras

Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras
Ronkonkoma
3.0 out of 10, (2 reviews)
"My sister got to the property before me and there were extra guests the owner of the property got in contact with me to let me know what was happening and told me to get everyone out or my stay would be terminated I got to the house and mad everyone leave . There was only 2 people in the house and my 2 year old son and he asked us to leave after he told me if I got everyone out I could stay. It was 1 am and I did everything he asked me to do. "
United States
Mitania L.
The price is AU$1,405
includes taxes & fees
27 Nov - 28 Nov
Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras

20. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is AU$788
includes taxes & fees
2 Dec - 3 Dec
Immaculate Waterfront 2 bedroom!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Shirley

Stroll along the charming Main Street, where local shops and eateries showcase the town's friendly small-town vibe. For outdoor enthusiasts, nearby Fire Island National Seashore offers pristine beaches and scenic hiking trails along the Atlantic coast.

A steel bridge with a pink sky in the background.

Top reviews in Shirley